Synthesis of photochromic 6-aryl-substituted bis(benzothiophenyl)- perfluorocyclopentenes by the Suzuki–Miyaura cross-coupling

Fluorescent Photoswitchable Diarylethenes for Biolabeling and Single-Molecule Localization Microscopies with Optical Superresolution

“…The low selectivity can be explained by the faster second step affording the product of disubstitution. Indeed, only one synthesis leading to an asymmetric and non-oxidized DAE possessing one aryl group (at C-6) and one halogen (at C-6′) has been reported to provide a good yield (over 50%, starting from the corresponding diiodide) . To overcome the problem of selectivity, we decided to start with an unoxidized and obviously less reactive C-6(6′)-diiodide “disulfide” ( 5-Me or 5-Et in Scheme ), build the dissymmetric cores, and oxidize both benzothiophene units at the final step.…”

“…Indeed, only one synthesis leading to an asymmetric and non-oxidized DAE possessing one aryl group (at C-6) and one halogen (at C-6′) has been reported to provide a good yield (over 50%, starting from the corresponding diiodide). 50 To overcome the problem of selectivity, we decided to start with an unoxidized and obviously less reactive C-6(6′)-diiodide "disulfide" (5-Me or 5-Et in Scheme 3), build the dissymmetric cores, and oxidize both benzothiophene units at the final step. After optimization, the Suzuki−Miyaura cross coupling indeed afforded the monosubstitution product, but only in moderate yields of 25−42%, when 1 equiv of the "first" boronate ester was applied in a mixture of THF/H 2 O (3:1, v/v), in the presence of K 3 PO 4 and SPhos/Pd(dba) 2 .…”

Synthesis, Photochromic and Luminescent Properties of Ammonium Salts of Spiropyrans

“…Spiropyrans form one of the most interesting classes of organic photochromic compounds capable of reversible isomerization under the action of external stimuli. The optical and other physicochemical properties of spiropyran isomers considerably differ; therefore, these photochromes can be used as sensors [ 1 , 2 , 3 , 4 , 5 , 6 ], optoelectronic and holographic devices [ 7 , 8 ], memory cells [ 9 , 10 , 11 ], etc. Moreover, an obvious advantage of spiropyrans over other classes of photochromic compounds is the relative ease of their synthesis and structural modification.…”

Synthesis, photo and acidochromic properties of spiropyran-containing methanofullerenes

“…The enhanced interest in these compounds is caused by their applicability for the development of promising materials and devices with unique characteristics: memory elements, [1][2][3] optoelectronic and holographic devices, 4,5 and sensors. [6][7][8][9][10][11] Spiropyrans are the best known and unique representatives of photochromic compounds, since they can be easily prepared and structurally modied and because of the possibility of targeted change of their spectral kinetic characteristics over a wide range. The isomers of spiropyrans considerably differ in their physical and optical properties, which inspired a number of studies on the use of these compounds as dynamic materials.…”